IP Library Granted Patent US 10,179,778
Granted Patent B2
US 10,179,778 · App. 14/040,587 · Granted Jan 15, 2019

Substituted aryl onium materials

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Quick Facts
Patent No.
US 10,179,778
App. No.
14/040,587
Granted
Jan 15, 2019
Kind
B2
Abstract

Acid generators comprising a carbocyclic or heteroaromatic group substituted with at least one diester moiety are provided. These acid generators are particularly useful as a photoresist composition component.

Claims (75)

1. A photoresist composition that comprises an acid generator that comprises a structure of Formula (I):a

wherein Z is a counter anion;

X is sulfur or iodine;

R 0 is hydrogen or a non-hydrogen substituent;

R′ and R″ are the same or different non-hydrogen substituents and optionally may form a ring, provided that if X is iodine, one of R′ and R″ is absent;

W is —C(═O)O(CX′X″)nC(═O)O—, wherein n is a positive integer and each X′ and X″ is independently a hydrogen or non-hydrogen substituent;

A is an optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group;

Q is optionally substituted alkylene, optionally substituted alkenylene, or optionally substituted alkynylene; and

E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent.

2. The photoresist composition of claim 1 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.

3. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 2 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

4. The photoresist composition of claim 1 wherein Z 31 contains a polymerizable moiety.

5. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 4 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

6. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 1 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

7. A photoresist composition that comprises an acid generator comprising a structure of Formula (II):

wherein Z is a counter anion;

R is —(CX′X″)nC(═O)OR, wherein n is a positive integer, each X′ and X″ is independently a hydrogen or non-hydrogen substituent, and R′ is a non-hydrogen substituent;

each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;

n, n′ and n″ are each independently 0, 1, 2, 3 or 4;

J represents a chemical bond, or a group capable of covalently linking B and C;

Q is a C 1 -C 8 saturated or unsaturated alkylene group;

E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent; and

A, B, and C are each the same or different optionally substituted carbocyclic aryl or heteroaromatic groups.

8. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 7 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

9. The photoresist composition of claim 7 wherein J represents a chemical bond.

10. The photoresist composition of claim 7 wherein J represents a group capable of covalently linking B and C.

11. The photoresist composition of claim 10 wherein J is optionally substituted alkylene group C═O, O, SO, SO 2 , NH, or NR where R is a non-hydrogen substituent.

12. The photoresist composition of claim 10 wherein J is an ether, ester, amide, carbonate, sulfortate, sulforte, or sulfonamide.

13. The photoresist composition of claim 7 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.

14. The photoresist composition of claim 7 wherein Z 31 contains a polymerizable moiety.

15. A photoresist composition that comprises an acid generator comprising a structure of Formula (IIa):

wherein Z is a counter anion;

R is —(CX′X″)nC(═O)OR, wherein n is a positive integer, each X′ and X″ is independently a hydrogen or non-hydrogen substituent, and R′ is a non-hydrogen substituent;

each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;

n, n′ and n″ are 0, 1, 2, 3 or 4;

R a and R b are each H, or R a and R b taken together represent a chemical bond or a group capable of covalently linking B and C;

Q is a C 1 -8 saturated or unsaturated alkylene group;

E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent; and

A, B, and C are each the same or different optionally substituted carbocyclic aryl or heteroaromatic groups.

16. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 15 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

17. The photoresist composition of claim 15 wherein R a and R b are each H.

18. The photoresist composition of claim 15 wherein R a and R b taken together represent a chemical bond or a group capable of covalently linking B and C.

19. The photoresist composition of claim 15 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.

20. The photoresist composition of claim 15 wherein Z 31 contains a polymerizable moiety.

21. An acid generator that comprises a structure of Formula (VII):

wherein

Z is a counter anion;

R is hydrogen or a non-hydrogen substituent;

each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;

n is 0, 1, 2, 3 or 4;

n′ and n″ are each independently 0, 1, 2, 3, 4 or 5;

E is hydrogen or a non-hydrogen substituent;

A′, B′, C′ are each independently a C 6 -C 36 aromatic, C 5 -C 36 polyaromatic, or C 5 -C 36 conjugated aromatic group;

J′ represents no bond, a single chemical bond, or a group capable of covalently linking B′ and C′;

R 5 is hydrogen or a non-hydrogen substituent; and

Q′ 3 is a C 1-8 alkylene group.

22. A photoresist composition that comprises an acid generator of claim 21 .

23. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 22 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

24. An acid generator that comprises a structure selected from the group consisting of:

25. A photoresist composition that comprises an acid generator of claim 24 .

26. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 25 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2016
From: LABEAUME, PAUL J., MR.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 040194/0507 →